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Jacquelyn Dalton

Dialogue in the Deep End: 5 Tips for Having Difficult Conversations on DEI

Updated: May 13

A woman holding a microphone in the front of a room of people

Have you ever felt like you're speaking, but no one is really listening?

That’s the challenge that many diversity, equity, and inclusion (DEI) leaders face. DEI dialogue is more than just talking and picking up new buzzwords; it involves navigating high-stakes conversations where every word counts. 


A significant opportunity for meaningful change in DEI is missed when the conversation stops before it gets started. Changes in future interactions, decisions, and, in many instances, how resources are allocated. 

If you are having a hard time getting the conversation going, don’t worry. This article explores five tips on how to have difficult DEI conversations, even in the most challenging rooms. 

As a DEI practitioner and frequent meeting facilitator, I often initiate discussions on topics like historical racism or current inequities—areas that rarely spark excitement or ease. This reality necessitates the use of effective strategies to keep everyone engaged, even when the subject matter is challenging. 


When I was starting my career in health disparities research, I experienced much trial and error when bringing up race-related issues. So much so that I had started to believe that DEI conversations should be reserved only for those as deeply committed to addressing racial inequity as I am. But, one day, while listening to a talk from 👑Claudia Rankine on navigating difficult conversations about race, I was struck by 👑Rankine’s belief that “every conversation about race doesn’t have to be about racism, and yet addressing racism is essential.” It dawned on me that maybe, just maybe, those failed conversations were me metaphorically pouring hot water on frozen glass. I wasn’t allowing the conversation to warm up!


a woman holding a microphone with one hand and pointing at a large flip chart of notes
Once I adopted 👑Rankine’s approach to DEI conversations, I was able to expand my ability to invite a more diverse audience into DEI conversations.

As I did this, one lesson learned was to consider the experience of individuals who are not DEI champions—individuals who are likely not prepared for, or even interested in, leading DEI-based conversations. Honestly, some have never openly discussed race or racism in public, let alone in the workplace or a classroom setting.


So, how can we effectively engage individuals or groups on topics like DEI, race, or racism?


Here are some strategies that have proven effective for me: 


  1. Let Go of Personal Bias: Yes, we all have biases, but they must be set aside in discussions about DEI. Replace bias with curiosity. Approach new or challenging topics with a desire to learn, asking questions rather than making judgments. 

  2. Establish Common Ground: At the core, anyone you talk to is a human being. Despite diverse backgrounds and experiences, try establishing conversations on neutral but meaningful topics. Engaging in meaningful conversation is a way to initiate trust-building. Plus, this approach demonstrates that our similarities and cultural differences often transcend skin color.

  3. Acknowledge the Broader Context: Recognizing that your primary concern is just one among many global issues is essential. In a world facing numerous crises, everyone may not see your urgent matter as their top priority. 

  4. Set Realistic Goals: Clearly define what you aim to achieve in each conversation. Set ambitious yet achievable goals within a reasonable time frame. This will make it easier for your audience to commit to actions and follow through. 

  5. Build Your Courage: Like any other skill, it just takes repetition. Regular practice can make these tough conversations feel more natural. Whereas not having the conversation only makes the issues worse. Sometimes, for the sake of being on the side of justice, you simply have to take the plunge into the deep end. 


These five tips can be helpful for any conversation, but in the context of DEI, they are vital tools in a much larger toolkit. Engaging in DEI isn't just about talking—it's about transforming. Each conversation is a step toward dismantling long-standing, systemic barriers and fostering a deeper understanding and respect across differences. 


As we implement these strategies, we do more than just communicate; we create a foundation for real and lasting change. Let’s embrace these challenging discussions not just as necessary but as opportunities to drive meaningful progress together. 


Like, Comment, and Subscribe! Share these tips with your colleagues so they, too, can have difficult conversations easily.  


In case you missed it: Check out my last blog post where I share the motivation behind my blog! 


Are you leading DEI conversations at school or work?

  • Yes! I am currently.

  • Yes, I have in the past, but not currently.

  • Not yet, but likely to start soon.

  • Thinking about getting started.


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